Design and synthesis of efficient electrogenerated chemiluminescent emitters derived from pyrene

MANGIONE, MARÍA I.; MORALES, GUSTAVO M.; MANGIONE, MARÍA I.; MORALES, GUSTAVO M.; CAPPELLARI, MARIA V.; MARZARI, GABRIELA; CAPPELLARI, MARIA V.; MARZARI, GABRIELA; SPANEVELLO, ROLANDO A.; FUNGO, FERNANDO; SPANEVELLO, ROLANDO A.; FUNGO, FERNANDO

JOURNAL OF THE ELECTROCHEMICAL SOCIETY

ELECTROCHEMICAL SOC INC

Año: 2018 vol. 165 p. 163 - 170

0013-4651

The design and synthesis of novel dendrimeric structures derived from a pyrene core with substituted triphenylamine and carbazole periphery demonstrated how molecular engineering allowed the fine tuning of the electrogenerated chemiluminiscence (ECL) properties. These two compound (Py-CBZ and Py-TPA) in comparison with the parent structures (Py and Py-Core) showed better chemical stability and anti-aggregation capability. At the same time, the photophysical (Absλmax, E00FLλmaxΦFL), photochemical (oxygen quenching), electrochemical (redox potentials) and optoelectronic (HOMO-LUMO gap and their energy position) properties were modulated, resulting in obtaining two highly ECL emitting molecular structures (Py-CBZ and Py-TPA). This study showed that functionalization of organic dyes with redox moieties (with the proper linker and position) improved the radical stability and also, modulated the optoelectronic properties with the concomitant enhancement of the ECL performance and their potential use in applications such as organic light-emitting devices.